Reflecting on a life when you chose to be a criminal; can you change?

Published on February 10, 2014
Jason Middleton. TINA COMEAU PHOTO

What makes a person the way they are? Why do people make the choices they do? Why choose a life of crime over obeying the law? Vanguard associate editor Tina Comeau sat down with Jason Middleton of Yarmouth to ask him these and other questions.



By Tina Comeau



Something bad happens in Yarmouth and Jason Middleton is the go-to guy at the top of most people’s suspect list.

He gets that. He’s not surprised.

Is it fair? Based on the life he lived, probably, he says.

Will it always be this way? Based on the life he’s trying to live now, he hopes not, he says. Other's aren't so sure.

If you’ve lived in Yarmouth for any amount of time you’re familiar with the name Jason Middleton, whether you’ve met him or not.

Middleton recalls once recently sitting next to a man in a bar. The man, not realizing whom he was talking to, was warning him about Middleton.

“That Jason Middleton is trouble with a capital T,” the man said, going on and on before finally asking the fellow seated next to him, “What’s your name?”

“It’s Jason Middleton,” said Middleton.

The man’s face suddenly got all flushed.

“It’s a good thing,” Middleton said to the man, “that I’m not that guy you were talking about.”

In other words, he may be Jason Middleton, but he says he's trying not to be that Jason Middleton anymore.

But how does a person become that Jason Middleton in the first place? The one who sold drugs? The one who spent a good part of his life locked up behind bars? The one who lived a violent past.

It’s a long story. One that starts out with a little kid growing up with his grandmother – Nan as he calls her – on Church Street, living in a house filled with aunts and uncles who felt more like sisters and brothers.

“I think I understood at an early age that we were poor,” says Middleton. “We went without a lot of things.”

But it wasn’t for lack of trying on his Nan’s part, he says, noting she worked more than one job. However it left many days when children were raising children in the household. Middleton would often tell his Nan that when he was old enough he was going to get a job and help out as much as he could.

Along the way his plan got altered.

For him, a pivotal turning point in his life is ‘that day.’ That day when he was on the front lawn of his Nan’s house and a car with workers from Children’s Aid pulled up. They were there to take him away. For a little boy, he believes he was 9 at the time, it was confusing. He was taken to a series of foster homes but he didn’t stick around, running away from one after another.

Eventually he was sent to the Nova Scotia Home for Colored Children in Dartmouth. You’ve probably heard about the stories of abuse that went on there. Middleton says he could tell you some stories of his own.

Already dealing with feelings of abandonment, anger and confusion, now add abuse to the list.

“I had no sense of belonging,” he says.

Later he ended up at the Shelburne School for Boys. Again, we’ve heard stories of what went on there. At the time nobody asked Middleton what his experiences there were.

“And I didn’t care to tell,” he says, finding solace instead with alcohol.

As a teenager, whose run-ins with the law also landed him in Waterville, he was learning tactics and strategies from those he was in custody with on how to make money.

Selling drugs? Not a bad job for a teenager he thought.

“I wasn’t really trying to have a lot of money,” he says. “I was just trying to have something to eat and a place to sleep and a pair of shoes without holes.”

Although, when in Rome . . .

Before long Middleton discovered it was easier in life to be angry and to act out. He also started stealing things. When he was caught the focus was on punishing him, not on trying to figure out why he was behaving the way he was. And so began a trend, he says.

“I didn’t know what I was going to jail for, but I knew I was going.” And now he wasn’t just surrounded in jail by others who had sold drugs or committed thefts. Some had stabbed people. They were serving time for violent offences.

And yet in the surroundings he often found himself in, Middleton decided that crime pays off.

Well, it pays off when you don’t get caught.

“When I started making money I could give my Nan some things. I could help my family with bills. It kind of intensified my criminality,” he says. “I didn’t like selling drugs, but it felt good to give them money.”

At the same time he was coming to terms with a visual impairment that he worried might one day leave him blind. He hadn’t done the things or seen the things yet that he wanted to. To do these things, he says, he needed money.


By the time he was 18, Middleton had decided he was going to be a criminal.

“I’m gonna be Scarface,” he says. “I’m gonna make a lot of money. At the end of the movie he gets shot but I’m not going to.”

He was smarter than that, he claims,  even if he was making really stupid, and dangerous, decisions. Ones that affected many others.

Eventually he made a decision that would not only be life altering for him, but life ending for someone else. And life changing for a family.

He and a friend got into an argument over drugs, according to the court, one June evening in 1993. The argument spilled onto the sidewalk . Middleton would take the man's life in the altercation.

According to the court record, Middleton insists he never intended to kill him.

“You didn’t think that by doing what you did it would kill him?” he’s asked now.

“No, I had done the same move to about 10 people before,” he says – a statement that is very troubling.

Middleton was charged with murder but pleaded guilty to manslaughter.

What he did was cause profound hurt to another family. And nothing he could ever do or say would reverse the devastation he caused them. Nor should it. It was horrible, and it was wrong.


At the age of 21 Middleton was sentenced to six years in a federal institution after pleading guilty to manslaughter. Because of his size and his behavior other inmates, he says, saw him as a “big, tough, aggressive black man.” And so he played the part.

“If I couldn’t be all of those things I would have hoped to be, aspired to be, tried to be, I’ll be this,” he decided. “And that’s what I became.” Others in the penitentiary were pleased with his decision.

You’re one of us now, they told him.

“I made some very, very bad decisions in my life,” he says now. Still, when he was released from prison after his manslaughter sentence it didn’t mean he was finished with those bad decisions – decisions that have impacted many lives beyond his own.

“I’m not stopping being a criminal,” he knew at the time. “I’m just going to be better with not getting caught.”

Any half-hearted attempt of turning his life around didn’t last.

Not even years later when he married and became a dad through that marriage.

He couldn’t escape his troubles with the law. In 2000 it was an extortion case. The media labeled him and his many co-accused the Sopranos, only without the charm.

His was never a good lifestyle. It was violent. It was illegal. It left many victims in its wake.

And Middleton and his friends were not immune. Friends who weren’t being charged with criminal acts were dying. His associates, his calls them.

“They’re gone and it’s not to terminal illness, it’s to homicide and to overdoses,” he says.

Middleton was sentenced to 18 months on the extortion charge and opted to remove himself from his family.

“I didn’t want to drag the family through this. I didn’t know anything about being a father.”

But he knew this about his son.

“I knew that I loved him.”


Cont'd on next page....



In 2003 Middleton was forced to face his own mortality when he was stabbed.

He nearly died, although many in the public wouldn’t have been saddened if he had. Or cared.

“Does it bother you to know that?” Middleton is asked. That doesn’t really bother him, but the stabbing still does.

While in a coma he remembers going to a place that was very cold and very dark.

“I remember praying to God, if you let me go back, I want to go back,” he says.

As he’s aged, he’s now in his early 40s, he doesn’t see himself as the man he used to be – or, at least, the man he doesn’t want to be. But trying to convince others of this will be a much harder sell. People who know his history, or have been touched by it, don't believe he will ever change. Nor do they think he deserves a do-over.

And the choices he made in life were his own. Nobody forced him.

“I’ve made some terrible, regrettable decisions in my life,” he says. “I knew better, but I still chose to do wrong.”

Many things he did were deliberate decisions. Others were for self-preservation. Better to be victimizing others than to be the victim yourself. He says he’s not looking to justify or minimize the things he’s done in life, nor is he looking to spread blame. He was bad. He did bad.

To those who heard of him, or came up against him, he was as tough as they come.

Then again, maybe not.

He might not have stepped away from a fight, but there are things that scare Jason Middleton.

“I’ve never been the nature, wilderness type of guy,” he says. “I don’t like squirrels. None of that stuff. I don’t touch gold fish. I don’t know why that is, it just is. Moths, they’re the worst of everything. They drive me crazy.”


While he was never going to become a doctor or a lawyer, Middleton still can’t help but wonder if his life would have been different had he never been taken off his Nan’s lawn that day when he was nine years old.

How different might other people's lives have been too if he hadn't chosen the life he did. How many people would have been spared hurt? Pain? Fear?

“Nan was busy working jobs, but in whatever capacity she could I know I got all of her love. Had she been a stay-at-home mom I would have gotten more. But she couldn’t be, she had to work two or three jobs,” he says. “Had I not come off that lawn, who knows what my life might have been?”

Can a person like him with the life he chose to live ever change? Many people, including victims of his crime, would say no. It's inconceivable, they say.

He says he’s trying to change, although a week after being interviewed by this newspaper he was in court to be sentenced on an assault charge. The assault was certainly serious enough that it caused fear and trauma for the victim involved.

But the Jason Middleton the court was told about this time was a different version of the one talked about in court in the past. His criminal record was discussed – it’s long, nasty and it’s anything by favourable – however a pre-sentence report, the court said, described a man who appears to have a willingness to change.

He has sought out treatment programs and community-based programs on his own the court was told. He is striving, his lawyer David Curry said, for betterment for the sake of his children. He’s taken steps to enroll in educational options at the community college level. He wants to volunteer with the local Needs to Deeds house. His lawyer says wants to help at-risk teenagers to learn from his mistakes.

At 41 years of age, the court was told, Jason Middleton is still a work in progress.

The judge called it a difficult sentencing. After all, this is Jason Middleton.

“He has lived a life where he has been subject to violence and engaged in violence,” said Judge Robert Prince. “Everything that we do and everything we experience influences who we are.”

After a sentencing hearing that went on for hours, Middleton didn’t receive jail time – likely one of the few times in his life that he was in a courtroom and wasn’t given a custodial sentence. He received a two-year suspended sentence, probation, a no contact clause with the victim and a lot of court conditions aimed at steering him on a correct path in life.

“His plan is one, that if it succeeds, will make life better for Mr. Middleton and for society,” the judge said.

Middleton, however, will be back before a judge on  March 11. He is charged that on Feb. 2 – just a couple of weeks after his last sentencing – that he breached terms of his probation by failing to abstain from the consumption of possession of alcohol.

Jason Middleton may never fully remove himself from the top of everyone’s suspect list when bad things happen. And for good reason.

He may never convince people that a person like him can change. Again, for good reason.

But, he's said at this stage in his life he wants to try.

Society will be the judge.